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Entry
CA00887                                                            

Classification
Carotenoid Name
Apo-10'-bixinal
IUPAC name Methyl-(9Z)-10'-oxo-6,10'-diapocaroten-6-oate
Formula
C20H24O3
Molecular Weight 
312.392 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9 including one aldehyde and one carboxylic acid methyl ester (9 in total)
Number of
conjugated multiple bonds 
9 including one aldehyde and one carboxylic acid methyl ester (9 in total)
Isomers 
InChI
InChI=1S/C20H24O3/c1-17(9-5-6-10-18(2)13-8-16-21)11-7-12-19(3)14-15-20(22)23-4/h5-16H,1-4H3/b6-5+,11-7+,13-8+,15-14+,17-9+,18-10+,19-12-
InChIKey
NXZZZYUALZNGOO-OKMAZBOSSA-N
Canonical SMILES
O=C/C=C/C(=C/C=C/C=C(/C=C/C=C(\C=C\C(=O)OC)/C)\C)/C
XLogP
4.904
Hydrogen Bond donors
(Lipinski's definition)
0
Hydrogen Bond Acceptors
(Lipinski's definition)
3
LipinskiFailures
0
Complexity of molecule
0.000
Number of heavy atoms
23
TPSA
(Topological Polar Surface Area) 
43.370 Å2
Source organisms
Bixa orellana (Ref.68, Ref.138, Ref.144) - Land plant: Bixaceae
References
  • Ref.68 : Haberli, Adrian; Pfander, Hanspeter, Helvetica Chimica Acta (1999), 82(5), 696-706., "Synthesis of bixin and three minor carotenoids from annatto (Bixa orellana)".
  • Ref.138 : Mercadante, A. Z.; Steck, A.; Pfander, H., Phytochemistry (1997), 46(8), 1379-1383., "Carotenoids from annatto. Part 3. Isolation and structure elucidation of minor carotenoids from annatto (Bixa orellana L.) seeds".
  • Ref.144 : Mercadante, Adriana Zerlotti, ACS Symposium Series (2001), 775(Chemistry and Physiology of Selected Food Colorants), 92-101, "Composition of carotenoids from annatto".
  • CAS
    201996-43-2
    Links to other DB
    KNApSAcK: C00023151

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